Benzyl 4-[cyclohexyl(formyl)amino]-2-[(2-methylpropan-2-yl)oxycarbonylamino]-4-oxobutanoate | 1050238-10-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: Benzyl 4-[cyclohexyl(formyl)amino]-2-[(2-methylpropan-2-yl)oxycarbonylamino]-4-oxobutanoate
• CAS: 1050238-10-2
• 化学式: C₂₃H₃₂N₂O₆
• 分子量: 432.517
• InChiKey: HLNVWSHUGBAEIQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  31
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  102
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  4-(benzyloxy)-3-((tert-butoxycarbonyl)amino)-4-oxobutanoic acid 、 N-环己基甲酰胺 、 4-methylcyclohexyl isocyanide 反应 0.5h， 以23%的产率得到Benzyl 4-[cyclohexyl(formyl)amino]-2-[(2-methylpropan-2-yl)oxycarbonylamino]-4-oxobutanoate
  参考文献：
  名称：

  Addressing Mechanistic Issues in the Coupling of Isonitriles and Carboxylic Acids: Potential Routes to Peptidic Constructs

  摘要：

  Mechanistic issues surrounding the two component coupling (2CC) reaction of carboxylic acids with isonitriles have been investigated. Experimental details suggest the formimidate carboxylate mixed anhydride intermediate exists in both interdictable and noninterdictable form. Furthermore, the 2CC reaction has been applied to the synthesis of a tripeptide featuring two formyl functional groups.

  DOI：

  10.1021/ja804709s

文献信息

• On the Two-Component Microwave-Mediated Reaction of Isonitriles with Carboxylic Acids: Regarding Alleged Formimidate Carboxylate Mixed Anhydrides
  作者：Xuechen Li、Yu Yuan、William F. Berkowitz、Louis J. Todaro、Samuel J. Danishefsky

  DOI：10.1021/ja8047078

  日期：2008.10.8

  Microwave induced two-component coupling (2CC) reaction of carboxylic acids with isonitriles gives rise to various N-formylamides. The formimidate carboxylate mixed anhydride (FCMA) is proposed as the reactive intermediate, which undergoes 1,3-O-->N acyl transfer to give the observed product. The formation and survival of the labile FCMA system has been evaluated.

  微波诱导羧酸与异腈的双组分偶联 (2CC) 反应产生各种 N-甲酰胺。甲酰亚胺羧酸酯混合酸酐 (FCMA) 被提议作为反应性中间体，其经历 1,3-O-->N 酰基转移以产生观察到的产物。已经评估了不稳定 FCMA 系统的形成和存活。